In the history of pedagogical thought, the problem of moral education appears as a complex process of the evolution of ideas about the formation of an individual’s moral qualities, reflecting changes in the socio-cultural conditions of various eras from antiquity to the present. The ancient tradition emphasized kalokagathia as the unity of the beautiful and the good, where the key virtues were courage, justice, temperance, and wisdom, aimed at educating a harmonious citizen, with distinctions between the Spartan military-patriotic and the Athenian intellectual-civic models. The medieval paradigm reinterpreted these ideas through a Christian lens, bringing to the fore the concept of sin, obedience, and religious instruction, which led to the predominance of authoritarian methods such as punishment and intimidation, alongside the development of forms of self-analysis and communal responsibility. In the Renaissance and early modern period, a secularization of approaches occurred, when educators such as Comenius, Locke, and Rousseau emphasized conformity to nature, the priority of morality over intellect, the natural development of moral feelings, and the balance between freedom and discipline. Russian pedagogical thought, synthesizing Western ideas with Orthodox values through the works of Ushinsky, Tolstoy, Makarenko, and Sukhomlinsky, emphasized the national character of upbringing, emotional sensitivity, collective responsibility, and influence on the individual through labor, beauty, and the word. Analysis of the dynamics of priority moral qualities reveals a shift from the military-civic virtues of antiquity and medieval piety toward the growing significance of compassion, tolerance, civic responsibility, and independence in the modern period, with an increasing socially oriented component. The evolution of methods demonstrates a transition from direct coercion and exercises in virtues to mediated forms through the mentor’s personal example, engagement in activities, the creation of an educative environment, and moral dialogue, which retain stable effectiveness. Institutional transformations reflect a decline in the role of religious and family structures alongside the growing influence of the school, the state, and especially the media environment in the digital age, which creates competition between traditional and new sources of value orientations. Philosophical-pedagogical approaches, including the rationalistic, emotional-sensory, activity-based, religious, and socio-cognitive, differ according to their sources of morality, mechanisms of formation, and effectiveness, with integrative models combining knowledge, emotions, and practice showing the greatest potential for the sustainability of results and adaptation to social changes. In the context of globalization, digitalization, and value transformation, historical-pedagogical analysis makes it possible to identify invariant principles, such as justice and personal example, as well as productive strategies for developing holistic approaches to moral education that ensure the unity of rational, emotional, and activity-based principles in personality formation.